narasin, 20-deoxy-, sodium salt → Narasin, 20-deoxy-17-epi-

HRID 46640Notes

Reaction equation

HRID 46640 reaction equation
[CH3:1][CH2:2][CH:3]([C:51]([O-:53])=[O:52])[CH:4]1[O:9][CH:8]([CH:10]([CH:12]([OH:48])[CH:13]([C:15]([CH:17]([CH:20]2[O:25][C:24]3([O:30][C:29]4([O:34][C:33]([CH:36]5[O:41][CH:40]([CH3:42])[C:39]([OH:45])([CH2:43][CH3:44])[CH2:38][CH2:37]5)([CH3:35])[CH2:32][CH2:31]4)[CH2:28][CH:27]=[CH:26]3)[CH:23]([CH3:46])[CH2:22][CH:21]2[CH3:47])[CH2:18][CH3:19])=[O:16])[CH3:14])[CH3:11])[CH:7]([CH3:49])[CH2:6][CH:5]1[CH3:50].[Na+]>C(OCC)(=O)C.O1CCOCC1>[CH3:1][CH2:2][CH:3]([C:51]([OH:53])=[O:52])[CH:4]1[O:9][CH:8]([CH:10]([CH:12]([OH:48])[CH:13]([C:15]([CH:17]([CH:20]2[O:25][C:24]3([O:30][C:29]4([O:34][C:33]([CH:36]5[O:41][CH:40]([CH3:42])[C:39]([OH:45])([CH2:43][CH3:44])[CH2:38][CH2:37]5)([CH3:35])[CH2:32][CH2:31]4)[CH2:28][CH:27]=[CH:26]3)[CH:23]([CH3:46])[CH2:22][CH:21]2[CH3:47])[CH2:18][CH3:19])=[O:16])[CH3:14])[CH3:11])[CH:7]([CH3:49])[CH2:6][CH:5]1[CH3:50]

Participants

4

Reactant 1

HCID 23698039narasin, 20-deoxy-, sodium salt

Product 1

HCID 3053530Narasin, 20-deoxy-17-epi-Yield 71.8%

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolventHCID 312751,4-DioxaneSolvent

Procedure

20-Deoxynarasin sodium salt (200 mg) was dissolved in ethyl acetate (10 ml). This solution was washed with 0.1 N HCl (10 ml) and then twice with water (5 ml). The resulting organic layer was evaporated to dryness to give a residue which was redissolved in dioxane and lyophilized to give 139.6 mg of 20-deoxynarasin free acid as a white solid.

Workup

  1. washThis solution was washed with 0.1 N HCl (10 ml)
  2. customThe resulting organic layer was evaporated to dryness
  3. customto give a residue which

Sources & evidence

ORD record
ord-a9a2ae4bc8604d3a80b456561e57178b
Source dataset
uspto-grants-1979_11
Patent number
US04174404

Reaction notes

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